Office Visit

For my years I have been obsessed about cross dressing. It seems like it's the only porn I watch. I have a collection of clothes and some toys.

I have always thought of finally hooking up with a man or another cross dresser but I was always too scared. Now I am married and that has definitely made it harder.

My wife knows about the dressing and once and awhile she will use a strap-on on me. But I have always had a desire to dress with someone else and try the real thing.

Now enter Matt. I have known Matt since he was a teenager, he is a very nice man, now in his early 30's who happens to be gay. In fact at my old job I got him a job there.

Matt would stop by from time to time at my job and say hi and we would catch up.

I noticed I would think about him when I would masturbate. I would imagine myself all dressed up on my knees sucking him off.

The fantasy's would continue with all sorts of themes me wearing different outfits and scenarios.

When I was horny I would always think to myself, that's it if Matt calls I am going to tell him to meet me and I am going to give in to my desires. After I would cum I would calm down and say I am not doing that.

Then one day I was sitting at my desk surfing cross-dresser and sissy videos rubbing my cock through my pants, I was getting bad thinking in my mind about sucking cock and getting fucked when my phone rang.

The receptionist called and said you have a visitor, can Matt come down to your office. My heart sunk, I said just give me a minute. I closed the computer, felt my paints to see if there was a wet spot from leaking cum and tried to calm down my cock.

I called my receptionist and said send him down.

When Matt arrived I gave him our customary hug but as I brought my arm around and I didn't pull it away from him as I lowered my arm I "accidentally" slide it over his crotch.

Matt says ooh I wont say anything if you won't. I could feel my face turning red and without even thinking I replied if you can keep your mouth shut maybe I will open mine. What??!! Matt said.

My mind was racing do I say just joking or is this it.

I shut the door to my office and said sit down.

Listen can I trust you? I mean really trust you? I mean if you tell someone, anyone I can kick the crap out of you?

Of course, you know you can trust me. I swear I will never tell a soul he replied.

I knew he had an idea of what I was going to say, he looked very excited.

OK, I said, I want to try it. Matt said, try it? Try what?

I think he just wanted to hear me say it.

OK Matt I want to try being with another man or at least sucking a cock, but I can't let it ruin my marriage it needs to be a secret.

His response was, OK let's go. I chuckled and said calm down.

I said there are somethings I have to tell you, if we do this I want to be a sissy. I want to wear lingerie and be the girl.

He did not know how to react at first, I think he was surprised, but he sounds that sounds fine.

I told him the office closes at 5, once everyone leaves I will text you and let you in.

I gave him a hug before i opened the door, this time I could feel both are rock hard cocks pressing against each other.

After a few I told my secretary I needed to step out, I ran home to pick out an outfit to wear. I ran through my stash trying to find something. I started to grab my leggings but I put them back thinking he is going to need easy access. So I grabbed my purple lace thong teddy and matching stockings. I put them in a bag a ran back to work.

I get back to my office and put my bag in my bottom draw, only a couple of hours to go. I could not concentrate about work I had butterfly's in my stomach. I kept thinking should I cancel, this is crazy, what am I doing.

Next thing I know I am hearing everyone saying goodnight and the lights are turning off before I could even think of changing my mind I get the text,"I am here".

Looking around the building two or three times making sure no one is here I let him in.

Follow me, we have to go to my office and stay in there because there are cameras in the hall ways. We get to my office and I tell him give a couple minutes to get ready.

I quickly try to get dressed, I was so nervous it took what seemed forever to clip my stockings up.

I called Matt in and his eyes budging he says mm look at you all in lace, look at the dick in lace. I stopped him and said I am sissy it's called a clit only real men have dicks.

As we hugged and I whispered in his ear do you want me to call you Matt, Daddy or master? I would love you to call me daddy and what is your name? It's Lindsay daddy.

Oh that's nice.

Daddy I am not sure what's going to happen, if I say stop I am sorry, you have to respect my limits. I have always wanted to be a man's sissy. This could be a one time thing, maybe it's not for me, I may want to be your booty call, if you need a blow job you could call me and I will take care of you. Who knows this maybe what I really want. You could come home one night to watch a cam show and see me all made up getting split roasted by two young studs. Well if that happens I hope I am one of the studs.

We start kissing, his hands running all over my body, tugging at my thong back, rubbing my ass and my lace covered clit.

I can feel his cock getting harder as I pull back he goes to undo his pants I said stop please let me unwrap my present.

I get down on my knees undo his jeans, slide them down and there was the bulge. This hard big bulge in these tight baby blue shorts. I was so nervous but anxious. I was no longer worried about being a man about to suck another man's cock but I was about to become a real sissy.

Watching all the porn I love when a woman pulls down her mans underwear and his cock slaps her face and I was hoping it was about to happen to me.

I slid his tight shorts down and I was was not disappointed his cock sprung out and slapped my cheek. Sissy mode took over I grabbed his cock and rubbed it all over my face and began to lick it all over. Matt's moans encouraged me to continue.

I started to jerk him slowly, I looked up at Matt and we looked eye to eye and both smiled. I was thinking this is it I am officially going to be a cocksucker.

I started to lick the head, twirling my tung all around then I slid it between my lips.

I just kept sliding my lips up and down, taking as much as I can and taking more each time. I kept trying to remember all the sissy cock sucking training and hypo videos i watched. My was rubbing my hair moaning yes keep going you sissy, your such a slut, mm keep going you cocksucker.

After a little bit Matt took his cock out of my mouth and told me to stand up. Oh no I thought I must suck at sucking cock.

He pulled me close and kissed me, I want it to last longer he said.

I said I want you to rub you cock all over me Daddy. I want to feel you cock rub over my lace covered clit and I want you to slide you cock into my teddy squeezing your cock and my clit and rub them together. I want to feel your cock on my ass, I want you to slide it in between my thong and my body.

He started to rub his cock all over the front of my clit, the feeling of his cock through the lace was amazing. He whispered how he loved the feeling of the lace against him. His slid his cock in my teddy and rubbed his cock against my clit, oh my what an amazing feeling I thought I was going to faint.

He turned me around rubbing his cock all over by bum, reaching around pulling my clit out and slowly jerking me. He started to simulate fucking me, his cock touched my balls and I let out a moan. He whispered in my ear you like that don't you? Yes Daddy.

He whispered let me fuck you, I was scared and said I don't know if I am ready. Oh please come on you need to try it, you never know if your going to get the chance again. You have come so far you started out the day as a man, then you became a sissy, then a cock sucking sissy (we both smirked) now you can become a woman.

His sweet talking reminded me of me with girls back in the day trying to get them to have sex with me. I started to know how they felt, I was thinking turn about is fair play I kissed him and said oh daddy I am yours.

He told me to lay down on my desk because he wanted to watch my face as I experience my first real man.

He started slowly, it hurt a little, as he was slowly pumping in and out he said it's OK sweetie your OK. He kept going slowly and deeper, I was starting to like it. Oh daddy I want your cock. He went from calling me sweetie to slut, whore and asking me how much I like his cock and how much I want him.

He pulls his cock out, comes over to my side and tells me to roll over on my side with his cock at my face while he is stroking it. Before I even know whats happening he shoots his load all over my face and in my mouth. Like a good girl I wipe all the cum onto my fingers lick them and lick the head of his cock.

I am now lying on my desk exhausted in a teddy with a raging hard on in front of the man who made me a slut.

I was hoping he would take care of me, as he is getting dressed he tells me to put on a show and play with myself. I rubbed my clit, licking my fingers circling the head and when I was about to cum I put it back in my teddy and came through the lace.

We started to clean up and get dressed, he asked me if I liked it, I said oh yes and maybe we will do this again just to make sure. Once we were dressed we walked out of my office and out the door like nothing happened.

When we got outside we hugged like normal until he whispered in my ear remember your officially a cock sucking sissy. He pulled away and said goodnight bud.

This is my first time writing a story. These are fantasies I have. If this story is OK with people I will do more. I am not a writer so please excuse my writing. Thank you.